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Captain Johnny is USCG licensed for sail and power. He grew up sailing, and has raced sailboats up and down the eastern seaboard. He has run tow boats and larger passenger vessels. In a small rural county in Virginia, he and his wife Amy taught English. He is currently working toward a South Carolina Master Naturalist certification. Asked what he likes most about these sailing trips on the Stiletto 27’s, he says, “Sailing a fast but super stable cat through a beautiful low country landscape is a blast.  But really, it’s meeting people from around the country and sharing a passion for being on the water that never gets old.”

a man in a boat on a body of water
a man sitting in a boat on a body of water


Originally from Long Island, NY, Captain Chris grew up sailing and racing dinghies in the shallow waters of the Great South Bay. He moved to Charleston in 2011 to attend the College of Charleston, where he studied English, and started working on boats after graduating in 2015. He is USCG licensed for sail and power and has experience on boats of all shapes and sizes, from schooners to tour boats, dinner boats, and small sailboats. In addition to his passion for sailing, Chris also loves music and gardening, and runs a blog called Extra Chill that is all about the local music scene.


Captain Richard bought his first sailboat (a 14’ sunfish his older brother had seen behind a neighbor’s barn) when he was 13 years old. After college he bought a 27’ sailboat on the Canadian border and sailed the eastern seaboard until he found and fell in love with folly beach where he dropped anchor in 2007 (with regular sails to the tropics during the winters). Richard now has over 200 Gulf Stream crossings and 500,000 sea miles under his belt but still prefers the local waters of Folly Beach and the surrounding islands. In 2023 Richard was awarded the designation of Coastal Master Naturalist. “My favorite thing about Sail Folly is the personal attention you can give the guests. Sharing my love of nature and sailing is so fun in these intimate settings.

a man with a hat on a boat
a man standing next to a body of water


Captain Matthew Chase grew up on boats, with the rhythm of the waves as familiar as his own heartbeat. He learned the lingo of port and starboard before he could even tell left from right. Spending his childhood sailing with his parents, he’s worn many hats in the maritime world—teaching sailing at summer camps, captaining fishing trips, and leading charters in Charleston, SC, and Key West, FL.

With a USCG 100-ton masters license in his pocket and a diploma from the College of Charleston, where he studied hospitality and tourism, Matthew’s all about sharing the charm of Folly Beach with others. He’s dedicated to ensuring guests aboard Sail Folly have a blast while staying safe and making memories to last a lifetime.